Life in a Glasshouse
by rbd32
Summary: Post S5 Finale. AU Future-Fic. Dan moves on from Blair and returns 20 years later to the city with his kids.
1. Chapter 1

Post S5 finale. AU after S6. Mostly future-fic with some back story, and flashbacks. Blair has a long way to go in self discovery in my opinion, she was just out right crazy in S5, it's the only way I can justify all of her actions. So Dan and Blair haven't seen each other in almost 20 years.

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Prologue:

When you've just gotten your heart broken, you can't focus on anything other than the pain that seems to radiate out of every pore in your body. Each morning you wake up after another night filled with nightmares, only to feel the ever present ache again. And you can't imagine the day it will ever go away.

But that is what time does for us. It doesn't heal the wounds, or make you forget entirely, it teaches us how to deal with loss. It's a lot like trying to lose weight, you can't see the changes from day to day but if you look back to where you started, you can't believe how far you've come. And if you do it right the past becomes muddled and you can't seem to remember all the details. But if you do it wrong, you gain it back and you carry it with you wherever you go.

In a lot of ways our mind is programmed to stop needing someone after so long of not being in contact with them. Most people who are granted the chance, to find closure, yell, scream, cry, and be heard, have it the easiest. Because after it's all said and done, you begin to replace old experiences with new ones, and you have new losses and new pain to deal with, covering up old wounds until they are barely recognizable.

However, some people don't have it so easy, our body is also programmed to remember that last, all consuming pain that changes our lives, when we don't allow ourselves anything to replace it with. When you aren't given the chance to grieve, or to repent, or to find closure, you become hard, you lose your full capacity to feel things so you're mind holds on to the last time you allowed yourself to feel completely. The result is, you don't grow, or change, or experience new things. You become bitter, hollow, and insensitive.

That was the excuse Dan gave himself when he wrote the sequel to Inside. He felt betrayed and full of anger. He could also hear bitterness, resentment, and downright hatred knocking on his door. He knew if he didn't get it out, everything he ever wanted to say, needed to say, he would hold on to it and it would utterly destroy him to the point where he may never be able to recover.

He poured every thought and feeling he ever had about the Upper East Side including Blair Waldorf and Serena Van Der Woodsen, into his novel, and then he waited. It took awhile, he had to take it day by day. But time worked in his favor, and he could feel himself start to open up again.

After his summer in Rome, he decided to stay the next year to finish his degree. While studying abroad, he had a few rebounds with women whom he could barely pronounce their name, let alone have a full conversation with. He managed to screen most of the calls from journalists wanting to interview him about his latest novel, the fact that he remained so elusive after it's debut made people even crazier about it. He had managed to read one article theorizing Dan Humphrey was in fact dead, taken out by the angry elitist families he had insulted. He laughed at that one.

Nate tried to contact him once, probably not to thank him for putting him in the book this time, and Dan couldn't bring himself to return the call. He never heard from Blair or Serena. A month after the book, Dan caught a glimpse of an American tabloid and in the bottom right corner is where he found out about Chuck and Blair's engagement.

After finishing his bachelors, he applied to the masters program at Yale and with the sales from his two previous books, and a generous scholarship, his money problems were a thing of the past.

He met Cassandra Davenport, his first month at Yale, she was a senior studying film. Her father, Dillinger Davenport, was a billionaire responsible for huge conglomerates around the world, an old money family that dated back to the founding of the city Davenport, in which Yale is so closely associated. He made Bart Bass look like a poor pauper. Her families' social circle was the epitome of pretentiousness. Dan had considered himself a slight snob previously, but this was nothing compared to the supercilious laughter that surrounded him at every dinner. Upper East Side elites couldn't hold a candle to that of the old money families' of Connecticut.

Dan found Cassandra to be warm and as passionate about film as he was about writing. In a way, she reminded him a little of both Blair and Vanessa. While she liked the finer things in life, she was also down to Earth and cared about other peoples happiness just as much as her own. Cassandra was the spitting image of her mother, Vera, with wild light brown hair with natural gold highlights, that fell down her back in curls. She had bright blue eyes that turned green depending on her mood, and curves that made every guy turn back for a second look. He couldn't stop himself from comparing her again to his past loves, she lit up a room like Serena, but she controlled it, like Blair.

Dan found his first impression of the Davenports' wasn't entirely accurate. They had a certain reputation to uphold but behind closed doors they were just as bit as warm as Cassandra. They were a tight knit family, they played games like Apples to Apples and had dinner together at least thrice a month. Her two older brothers, Jeffrey and Piers, worked with Dillinger, and had begun families' of their own. After the perfunctory big brother speech, they gave him a beer, and teased him about his lack of athleticism. Her father was regular news, usually in the press about his ruthless business practices, but somehow they managed to keep the important things private, as if they all enjoyed keeping up the pretenses if it meant having this secret, and Dan fell in love with Cassandra even more.

Dan didn't mind the public dinners or galas after that, as they spent many nights rolling their eyes and sniggering with laughter as they heard the names of Philip Glass, Rachmaninov, and Wordsworth mentioned in every conversation. They couldn't pass a group of ladies without someone mentioning "have you heard the news, Sally Dirven's husband has taken to the bottle again." It was always "news", never gossip.

They made these obligations into private jokes of who could sound more like a prat. Cassandra always won having grown up around it. She could have a twenty minute conversation about a glass of wine, spewing out mounds of bullshit without anyone ever calling her on it.

"A sublet hint of backne, stimulating the palate without overpowering the excessively large fupa undertones."

She had a way of raising her eyebrows anytime anyone looked at her peculiarly as if they would spontaneously combust for questioning her and they quickly scurried away.

Dan gave her a run for her money as he would ask every host about the price of his house, feigning obsessive interest in the property market, and going on about the desirable areas in which he planned to buy, as soon as he was done with school and how he was so disappointed in the lack of style of the dormitories. He added words like vastly and proverbial to every sentence.

Sometimes they would catch a disapproving look from Dillinger or Vera, and then the twinkle of their eye would reveal they were laughing on the inside. For the first time in a long time, Dan pictured what the rest of his life would be like with a girl, and with Cassandra, he liked what he saw.

Despite the press and the prestige that surrounded Cassandra's family, she managed to find a group of close friends whom she could drink beer, eat pizza, and still talk about literature, film, and music, without mentioning Shakespeare or Russian classical. Since Cassandra had been there for four years, their group was private and exclusive, and Dan fit a hole they hadn't realized they had until he was there. They were the first real friends Dan had made since Vanessa, they made him feel like he had known them his entire life.

Dan started watching football, adorned in a Yale sweatshirt, tailgating before every game. He was a staff columnist at the Yale Daily News. His friends introduced him to all of the Yale traditions, and three months into the school year he abandoned his dorm and moved into the spare bedroom in an old Victorian style house on Old Campus, that all of the guys shared. He was busy all the time, and he loved every minute of it.

He shied away from telling people he was a published author, but people found out and questioned him about Inside and Exiled every where he went. It was the subject of his and Cassandra's first, second, and third fight. They spent a lot of late nights discussing Gossip Girl, and the destruction that seemed to follow anyone who got mixed up in the Upper East Side who didn't belong there. She was fascinated and appalled by his stories, refusing to believe how much of his novels weren't actually fiction.

The first fight they had was because she took Blair's side over his. She called him a judgmental prick for using Blair's real life tragedies for his personal gain. She didn't understand how he could write such beautiful things about her and a year later, completely degrade her. She thought it was obvious anyone who suffers a miscarriage is allowed a free pass, that any girl in their right mind would be utterly confused. She questioned his morals and his definition of love because surely he didn't know the real meaning if he could publicize her dirty laundry so abhorrently just because she had left him without a goodbye.

He told her his reason for writing it, how often Blair had reassured him that he had nothing to worry about, and he refused to admit he was wrong. She took it as a sign that if he still felt that strongly about it than he must not be over her. That ignited fight number two.

When she suggested he write her an apology, the third fight was the worst. He tried to reason with her by telling her Blair probably hadn't even read the book, she used him, didn't care about him, and besides it had been over a year. She told him that it wasn't the point, and not to speak to her again. He was distraught and confused for two days until she showed up at his door at two am, tear stained cheeks. He hoped it was the last conversation they would ever have about Blair. Without any sleep, they walked to the nearest blue postage box, and sent the letter.

Rufus and Jenny had visited over Thanksgiving, and took an immediate liking to Cassandra. Christmas came and went, Dan spent a week in Switzerland, skiing with the Davenports'. He and Cassandra had never been better. The next few months followed in similar fashion.

Rufus and Lily got remarried around Easter. It was a quiet ceremony, in upstate New York. After a very confusing process of helping Chuck win back the Empire, Lily divorced Bart, and spent the rest of the time trying to prove her love to Rufus. They had been back together for almost six months. Dan tried to keep his disapproval from showing but it wasn't until he saw his long lost family gathered in front of him that he finally let it go.

He hugged Eric until he couldn't breathe. And he was overtaken with relief when Serena ran to give him a hug, forgiving all the history between them in that moment. Nate was at her side, silent and cautious. Dan held out his arms as Nate laughed and clapped him on the back. Dan never let go of Cassandra's hand for more than a second. She and Serena connected immediately, as expected and the entire night went better than okay, it was incredibly drama free for a Rhodes-Van Der Woodsen- Humphrey affair. Chuck and Blair were suspiciously absent. Dan and Cassandra returned to New Haven, more in love than ever.

In May it had been almost two years exactly since he had left the Upper East Side, and on the day of graduation, Dan asked Cassandra to be his wife, and when she accepted Dan could not be happier.

Present:

Seventeen years later, and if you were to ask Dan Humphrey about the time Blair Waldorf broke his heart back when he was twenty one, he would have a hard time remembering the who, what, where, when, and why of it all. He'd be lying if he said he never thought of her, he's seen her name in magazines, heard it mentioned on t.v., and he thought he saw her once in a crowd. He wonders if she got her wish, to be happy. But apart from those few moments, he hasn't felt the need to reminisce over their turbulent years spent being enemies, then friends, then lovers, ever.

That was until, he ended up back in New York City of all places, a single father, and where better to send his children than Constance Billard School for Girls and St. Jude's School for Boys.

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Thanks for reading! I know this chapter was a lot of back history, the next chapter probably will be too explaining how Dan got to this point in his life. Eventual back history for Blair. Eventual Blair and Dan interaction because I do love them.


	2. Chapter 2

He can't believe he's already been back in the city for three months. It's nearing 10 p.m. and Dan should be exhausted. Another week is over, and he's worked another fifteen hour day at The New Yorker. He is editor-in-chief, and while the last three months have been demanding, he hasn't felt this invigorated in years. He wasn't ready to go home, the kids were out, so he didn't stop at 62nd street when he saw his home; instead he continued up 5th avenue letting his thoughts wander.

There is one thing that Dan knows for certain being back in the city for nearly three months now, the Upper East Side doesn't change for anyone, and time was no exception. In the last twenty years, the rest of Manhattan and the outer boroughs were interested in accommodating the trendsetters, adapting with the culture. People were interested in finding the next SoHo, TriBeCa, or Park Slope's in places such as Bushwick, Prospect Heights, and Flushing. The five boroughs had reunited in trying to shape new communities, like finding neighborhood coziness in Flushing, and new foot traffic for fashion retailers in The Garment District. Far West Midtown and Morningside Height's relationship with the Upper West Side had continued to remain fluid and the rehabilitated waterfront had been a catalyst to both commercial and residential venues. The bohemian subculture had branched out from Williamsburg to Chelsea, keeping responsibility for New York's art industry and nightlife.

Many people would say the Upper East Side was outdated, stodgy, and no one fashionable could love it. These people didn't understand, the Upper East Side was not interested in being the next "juicy" neighborhood. The Upper East Side doesn't care about up and coming, it relies on tradition, and primarily proximity. The rest of New York City could lay claim to whatever and wherever they pleased, the Upper East Side had been refined long ago. You could argue it wasn't architecturally impressive, but it had a taste for finery like no one else, home to many cultural institutions, private schools, and Madison Avenue. The chic boutiques that lined Madison Avenue could give any neighboring district like SoHo or Flatiron a run for it's money. The Upper East Side had longevity, and Central Park.

Being here was like stepping back in time. Even though the boutiques changed names, old town houses were renovated, and new structures were built; the culture hadn't changed and the people were still snobbishly clueless. And yet, Dan felt like he was coming home. His sixteen year old self would die before ever admitting this, but there was something that had always drawn him here. Maybe in a world where people are ever-changing, where it's so easy to lose yourself, it's refreshing to see somewhere hold so strongly to it's roots, even if they were wealthy outdated ones.

He could still be a stubborn guy, and although living in the Upper East Side was no longer the end of his world, back in April when he started looking to buy he wouldn't allow his realtor to show him any places farther north than 66th street. In May, two weeks before they moved, he finally put an offer in on a split penthouse on 5th Avenue at East 62nd street. Dan Humphrey was an Upper East Sider, and his house was three streets over from almost being called Midtown. He could rationalize that. The location couldn't be more perfect. It was less than a two mile walk to The New Yorker offices and 20 blocks from Constance and St. Jude's, which was just over a mile away.

His building was fourteen floors, housing 40 separate units, the top two floors were dedicated to the two duplex style penthouses. Each one had it's own private elevator access, 4,000 sq. ft including the garden terrace just off the den on the second floor. The entire building's occupants had access to the roof, that overlooked the southernmost part of Central Park. It was four bedrooms, four baths, and just right for Dan and his three children, even if Teddy wouldn't technically live with him anymore in the fall. And it cost a pretty penny, coming in at 10 million dollars.

Dan stopped when he got to 81st street, and looked at St. Jude's and Constance Billard standing to his right, still unfaltering as ever. Back in June when he set up a few meet and greets with the Dean for Faye and Paul, he would have said the buildings seemed smaller, less daunting, than he remembered. But tonight he's not the experienced world traveler, the widely known and established author, or the former husband of celebrity director Cassandra Davenport. He is Dan Humphrey from Brooklyn. And in that way, it's the first time he's been back here. And tonight, New York City is as big as he remembers, intimidating, and full of mysteries.

He knows Faye and Paul won't have any trouble making friends or fitting in here. That's what they've done their whole lives, moving from place to place, country to country. They were nomadic and adaptable. And he think it's kind of ironic, that he lives on the Upper East Side, and all his kids ever seem to talk about is why they can't live somewhere hipper like Williamsburg or Chelsea.

Over the last three months, when he didn't have to work, he took them to all of his favorite spots like Housing Works Bookstore Cafe, a used bookshop that is a must for New York writers; Valselkas for pierogis, and Cafe Habana for sandwiches. Rufus came with them to The Front Room Gallery in Williamsburg, and Communitea; the cafe Vanessa first worked at near the loft. He took them to places he had grown to love like Geisha sushi, Sotheby's, and Henri Bendels. They spent entire days at the MoMA, and the Guggenheim. They had decided to dedicate the first Saturday of every month attending entertainment at the Lincoln Center for a performance whether it was opera, theatre, or the orchestra.

He crosses the street to sit at the MET steps. There were still quite a few people lingering at this time of night and he stays on the left side near the bottom. He was working when Teddy and the twins spent the day here last week, and he was strangely okay with it. This was the one place in all of New York City that could strip away the last 20 years from him, bring back his insecurities, and old memories.

It had been awhile since he allowed himself the time to take stock of his life. He believed with all his heart you had to stay in the present to be successful. So he had spent his life starting each day with intent and clarity. He had raised two intelligent kids, had a great career, and supportive friends. He had done everything right, and yet, he was alone. He knows he has changed in a lot of ways. He doesn't talk in run-on sentences when he's nervous nor does he jump to conclusions; he's more understanding and patient. He learned the hard way to stop blaming his problems on others, something he will probably always struggle with. He's a little more cultured and a little less charming.

One thing that hasn't changed, he is still a diehard romantic. He believes in grand gestures, and even more in the small ones, to relay his true feelings. He still watches old movies, loves conversation, and writes about the women in his life. But somewhere he lost that connection between his intellect and his heart. His sensitivity to the beautiful, spiritual, and sublime; that sensitivity that made him feel things deeply. He's not sure when or where he lost it either. Tonight is a special night, and he doesn't stop himself from looking back.

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By the time Dan had left New York almost 20 years ago, he had gotten more comfortable with accepting other's good fortune without feeling like he had to be self-righteous about his families' hardships. By the time he had graduated Yale and accepted a job offer at one of the highest selling newspapers in Connecticut, he was no longer smug and earnest about drawing a line between himself and those wealthier than him. Besides, his fiancé had a trust fund three times the size of CeCe Rhodes' entire inheritance. Dan admitted to his fear that his career would never be enough for her if they always relied on her wealth to support them. She was afraid he would always refer to it as "her wealth and never ours". He teased her about her father's need for a prenup if that's the way she felt. In all seriousness, he told her he would try to work on his insecurities. She promised to try and always support him and make him feel validated.

They were married on October 1, 2014, at her family's estate in Davenport; it was their one year anniversary. It was a beautiful and clear, fall day and the leaves were a variety of red, orange, and green. 300 people were in attendance, and reporters lined the gates, trying to catch any shot of the harvest themed wedding. Dan asked Rufus, Eric, and his college friends from Yale to stand up with him.

Most all of Dan's friends and family were in attendance. Blair's face flashed in his mind, and just as quickly as it had come, it was gone, and he said I do. Cassandra surprised him by inviting Vanessa Abrams. They had made up through phone calls and e-mails while he was in Rome, but they were never able to re-establish a consistent friendship again. Seeing her was a welcomed surprise. Coincidentally Nate was single and he spent the entire night catching up with her.

Serena showed up with Carter, with news that they were engaged and expecting. Dan was pretty sure he was Serena-shockproof because he didn't even blink twice at the news. He remembered thinking how easy it was to forget everything that happened between him and Serena. If he was being honest, he just hadn't cared a whole lot to stay angry with her, it was never about her anyway. She would always be beautifully lost, wandering around, trying to find something to ground her. She seemed better though, she had that familiar lightness that he hadn't seen in many years, and she was genuine when she wished him a lifetime of happiness. He hoped she had finally found what she was looking for.

The twins were born on June 15, 2015; a beautiful boy and girl. Paul Dilinger Humphrey had his father's nose and his mother's chin, a mass of dark hair, and striking green eyes. Faye Cordelia Humphrey had her father's eyes and her mother's full lips. Dan wasn't prepared for the amount of love that consumed him the day he held his children for the first time, both for them and his wife. Cass had never been more beautiful to him.

They left Connecticut after three years to move to California. Dan quit his job at the paper, and became a full time dad while Cassie became more involved in directing. The next year was the beginning of the "Golden Vagabond Years", as Dan referred to them later. Cassandra Davenport had begun to make headway in Hollywood, attracting admirers and critics alike, and her career took off. They kept their home in Los Angeles, but for the next six years they were vagabonds, moving from one city to the next, flying over oceans, or shuttling from country to country by boat.

They brought Bridgett, their nanny and certified tutor, along with them, and Faye and Paul were home-schooled. They learned to speak the romance languages from exposure, and geography by mapping out their temporary homes. They kept in touch with the Humphreys and the Davenports back home through letters and postcards. They studied local culture wherever they went, and studied everything else on-set only twenty feet away from international movie stars. Dan and Cassie made sure they had every opportunity at their disposal while also keeping them grounded by not allowing smart phones or personal laptops until they were thirteen. They were given a small allowance, that they usually spent on little mementos they sent back to California for safe-keeping, that reminded them of the places they had been.

He loved spending every minute of the day with them. Paul was bright-eyed and curious, impressionable, and unabashed. Faye was more reserved, perceptive, and wise. They balanced each other out, pointing out things the other wouldn't have noticed, pushing the boundaries of their personalities, which served to strengthen them as siblings and as people in general.

They made friends wherever they stayed, and brought along the old ones. Eric and his partner, and Jenny and her husband, would come and visit them whenever they were in Europe. They made a tradition of renting a chateau in Switzerland each Christmas, inviting the entire Humphrey-Rhode's family and the Davenports. They saw their college friends whenever they came back to Connecticut. They vacationed with Nate, Vanessa, and their children in Australia, and again in Thailand two years in a row. Serena and Carter made it to Christmas every year.

Dan's last book was published a year after the twins were born. It was a transition period for him, and he struggled the whole way through it. People were expecting something sharp and self deprecating. The one he wrote was forced and dulled around the edges. It wasn't received well and it took Dan until three months into their globetrotting, for inspiration to strike again. The idea came to him for a young adult series. It would be called The Vagabond Twins.

He spent another six months making the blueprints, outlining for six novels, and writing the first installment. Cordie and Dillin, were twins who grew up as vagabonds, traveling the world with their famous mother. The twins are devilishly smart, rebellious, and quick witted. They are each others best friends and they have a Polish nanny, Elza, who serves as their loyal sidekick with a witty repartee. On their eleventh birthday they discover an ancient artifact that has magical tendencies. They are able to travel back in time but are confined to whichever city they are in at the present time. At first it's all fun and games, but they soon discover there is a whole other world around them, living in secrecy. They are hunted by an enemy that remains hidden, stumbling upon ancient prophecies and famous people they read about in history books who know more than they should. They make life long friends, lose loved ones, and learn a whole lot about growing up.

The first novel was published when the twins turn 5. It didn't take long for both, kids and adults, to fall in love with his story. He continued to publish one every year on the twins birthday, his gift to them. They are delighted, even if they don't quite understand them yet. Cass is the most excited of all, she gushes about them to every person who will listen. She tells him how proud she is to be married to a man who can give their children the gift of words, better than any monetary object. They have so much fun on the first book tour, traveling for six weeks promoting it, that Cass makes sure to schedule her projects around the releases each year.

By book five, Dan's series had a cult following. Over 50 million copies in print in 30 different languages, and the number was growing every month. The movie rights were in negotiation for an entire year before being finalized to start the six-movie, franchise as soon as the sixth book was published. Dan had already finished writing it but it wouldn't be released until June 15th of the next year.

They were living the high life, and Hollywood loved to label them "The Vagabonds" as they were photographed coming and going from award ceremonies, movie sets, or bookstores. The twins had just turned 10, and Dan had loved his wife for almost 12 years.

In the 10 and a half years they had been married, Cassandra continued to grow stronger as a wife and a mother. She never stopped moving, working all hours of the day, while finding time to spend with her kids as well. She was doing what she loved with the man she loved, and the children she would die for. She and Faye shared a special bond when it came to being on set. Faye had an eye for detail, she could sit for hours watching and helping the crew set up the film sets, picking out small components that helped complete a room. Cass and Paul were most alike though, they were the adventurous ones, always first in line to go on an excursion to some place new and exotic looking.

Cass and Dan didn't have a lot of time to themselves after their children came and their careers took off. Things were good, and they had no reason to complain. They didn't notice when they became more passionate about their careers than each other. They were so busy leading fulfilling lives they forgot to take the time to hold hands, cuddle, and connect on a deeper level.

But when Dan no longer had his series to focus on and Cassandra was in-between projects they finally noticed something was lacking. They tried not to fight about it, but Dan was never good at being at fault. He blamed her for working too much, and she couldn't believe he had jumped down her throat when they both had demanding jobs. She ended up giving in, agreeing to finally go home, settle down, spend time together, alone. They moved back to Los Angeles right after Dan's fifth book tour was done.

A week after being settled in, they had a surprise visitor. His name was Teddy Chase, and he was 16 years old. And he was claiming to be Cassandra's son.

* * *

Dan wasn't aware what had shaken him from his thoughts. But he looked around and saw most of the lingering people had vanished. He was getting up to start his walk home when he saw a woman sitting on the far east side, with her back to him. It was the same spot he had seen Blair and Serena sit so many years ago. He wondered if this was just an illusion, and couldn't stop himself from moving forward.

He came up on her left, her head turned in the opposite direction looking out, lost in thought. He found it incredible that with more than 2 million people living in Manhattan now, they were the only two people here in this place, at this time. And then again he thinks he knew from the moment he left his office tonight, that he would somehow end up here. He doesn't remember how he heard, but someone said she was in Paris working for the summer, and would be back before the fall. He wonders if he should just stop now, turn around and go home. It's been nineteen years since they spoke, they are basically strangers. But tonight, he is Dan from Brooklyn, and that's how he rationalizes what he says next.

"If I squint just right, it's like were 16 again, and you've just dumped yogurt on a some poor unsuspecting girl."

He's standing three steps to her left, and she jerks her head towards him at the sound of his voice. She stares at him for a few seconds, and for a moment he thinks he's made a mistake. It's been too long.

But then recognition pools in her eyes and the corners of her mouth turn upwards just a little.

"Make sure to keep your eyes wide open then, I would hate to have to send you home for wearing that hideous tie." Blair tells him as she nods her head at his attire.

He laughs out loud and sits down next to her.

"So when-?"

"Shhhh. Don't ruin it with your excessive talking."

She says to him smirking, with her big brown eyes. He thinks Blair Waldorf still has the most expressive eyes of any woman he has ever met. He almost objects but he doesn't. Brooklyn Dan always gave in to her, was in awe of her, and more importantly understood her. Whatever feeing that drew him here tonight, was the same that brought her here too.

So they sat there, unmoving, for ten minutes, maybe more, maybe less. Out of all the places he had lived, there was nothing that compared to New York City. He wonders why it's taken him so long to get back here. And maybe tonight is the city's way of welcoming him home. Maybe it's the same for Blair too.

"You know, when I squint just right, I'm not 16. I'm 21 and it's my last day as a princess." Blair speaks softly and stands up afterwards.

Dan feels it as soon as she does, the moment is slipping away and Brooklyn Dan along with it. He is momentarily dislodged by her confession, he can't remember her ever being forthcoming like that. A part of him is remembering a day nineteen years ago, seeing her in a pink dress with a plastic tiara. And the other part is looking at her like he doesn't know her anymore, maybe never at all. He stands up too, but he doesn't speak and it's like she notices the inner conflict taking place because she doesn't wait for a reply, instead she starts to walk down the steps toward home.

He's still standing there, awkwardly with his hands in his pockets. At the last step she turns back to him, and her tone is a little more forced but as expressive as ever.

"Welcome home, Dan."

He can't tell if the way she says it, with that devilish glare, is meant to be prophetic or a threat. He decides it's a little of both.

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**Thanks for all the feedback and the followers! Let me know what you think. Happy Labor Day!**


	3. Chapter 3

Maybe Blair could have forgotten Dan Humphrey if he didn't write a scathing novel about her and run away to Rome never to be seen again for twenty years. She may have been able to forget him if he would have answered any of her phone calls or e-mails trying to explain why she chose Chuck Bass without telling him first. She may have been able to forget him if she hadn't seen the video of him and Serena having sex at the Shepherds divorce party. But she can't forget him so she uses those things to reassure herself that she made the right choice in leaving him. She uses those things so she doesn't remember the real reasons she doesn't _want_ to forget him.

She devotes all of her time and energy into going after what she thinks she wants. She hasn't been able to let go of Chuck for two years and yet she was always finding excuses for why they couldn't be together. It had finally taken her relationship with Dan to realize she could find herself again, and before the tiara, and the Empire, she had been set on Chuck. How could she not choose Chuck when everyone had always said they had this force field between them, drawing them back together. They were magnetic and inevitable.

But when she finally tells Chuck this, he is angry with her, and he tells her she's not enough, not now, when he's lost his Empire, again. He's spent the entire year waiting for her, so it only makes sense that now that she's ready to commit, he's changed his mind. She refuses to look at the irony of being rejected on the same hotel she was sold for two years ago. But she convinces herself that he has every right to be angry, she has been fickle and cold. He did buy her freedom, and he does always put her first, right? She's already decided this is what she wants, and so she doesn't bother addressing the tiny doubt that has been seeded deep within. She flies to Paris with her mother, and again to Monaco, to fight for what she wants.

Chuck is impressed with her because he doesn't reject her a second time and they reunite, ChuckandBlair, BlairandChuck. But then, he decides in order for them to fully commit they need to take time by themselves. Time to find out who they are and sort out their issues separately because this time, there is no turning back. Blair finds herself comparing him to Dan, the Dan who told her they were a team and they needed to face issues together. She wonders why he hasn't replied to a single e-mail. And then Chuck gives her his ring on a necklace and she forgets about everything else.

The summer passes, and she's barely seen Chuck or anyone else from New York. She spends all her time in Paris working hard as she job shadows Eleanor. She never imagined herself on this side of fashion, was never particularly interested in the ins and outs of the design aspect. If she's honest with herself, she finds it a little boring. She loves fashion, and learning about design is a great asset to have but she wants more skills to add to her arsenal. She needs a challenge, and more control. She ends up spending most of her time with Eleanor's business partner, who manages the company. She's already good at staying updated on trends and fashion news. She already has pristine taste and a qualified opinion. So she learns about marketing, advertising, and merchandising. She surrounds herself with the entire industry, introducing herself to photographers, writers, designers, and editors she meets in Paris.

By the end of the summer she has promises of future employment if she comes back with her diploma. They all tell her she has potential but she needs to finish college, and without it all they can offer her is an internship or entry level positions with little hope for promotion. Eleanor isn't exactly surprised when Blair confides in her that she isn't ready for the reigns to Eleanor Waldorf Designs, that she is going back to Columbia. Eleanor calls her a dictator of taste and Blair smiles when it reminds her of Dan. She may be that same powerful and intelligent girl after all.

She's surprised by how much she thinks of Dan. She misses him, almost calls him every time she needs a friend, pretends like she knows his exact opinion and what he would say when she watches old movies when she's alone at night, or goes to art exhibit on the weekends. He has become the voice inside her head.

Chuck tries to be happy for her and her rejuvenated sense of spirit and motivation. He hasn't had any luck with investors and Bart cuts him down at every turn making him feel like the same little boy who tried his entire life to get his father's attention. He isn't anywhere close to getting what he wants or figuring out his issues. He doesn't accept Blair's help when she offers and she somehow asks herself if Chuck does it on purpose, he knows that she needs to be needed and by rejecting her help, he has some sort of power over her. She wonders if he's still playing a game with her. But then he tells her he loves her and he can't wait for them to be reunited, and she forgets to answer those questions.

Blair hasn't heard from Serena all summer, Gossip Girl hasn't reported anything on her, and when Lily calls concerned that she hasn't heard from her, Blair starts to worry. She doesn't understand it, why she feels this need to come to Serena's rescue. She hates that she likes being the successful one, seeing Serena lose control. She hates it because it might mean the one thing they were always so afraid to say out loud. Their relationship is more toxic than good.

After one week of being back in New York City, Dan's book is released. She reads it right away and she wishes she hadn't. She drowns his voice inside her head until she can no longer hear it. She is angry with him but she convinces herself that Dan Humphrey is still a judgmental ass with a chip on his shoulder who plays the victim better than even Serena, and she shouldn't be bothered with his opinion of her. It just proves she made the right choice after all.

She can tell Chuck reads the book even though he doesn't bring it up. She can tell because Dan's book is from Charlie Trout's point of view and and no one is painted more conniving and damaged than the main character. Charlie and Clair's relationship is in print for all the world to read, and Charlie Trout might as well be the devil. Clair is insecure and emotionally unstable after jumping from one relationship to the next, suffering a miscarriage, and running back to Charlie every time she comes close to maturing or moving on. The two of them exile everyone in their path, whoever dares come between them, or speaks the truth. But when they finally get together, it's not enough for Charlie, and he realizes he is incapable of happiness and he commits suicide. Clair is left alone in the city, everyone she used to care about has been exiled.

Chuck can't fix things with Bart but he can prove Dan Humphrey wrong and he decides he doesn't want to play the charade of being apart any longer. So when Chuck proposes a week later, she says yes.

Falling back into her old life is a lot easier than she thought. She has always been a master at living in denial, so good in fact, that she pretends so well she actually starts to believe it. They rescue Serena from herself again, flushing the drugs down the toilet, standing watch for 48 hours. In no time at all, Blair and Serena are back to their lifetime bond of holding on too tight while passively resenting one another.

Blair schemes with Chuck to get back at Bart. She possesses minions and manipulates those around her at Columbia to stay in control. Her and Chuck fall back into a routine of second guessing each other, arguing, and making up with sex instead of talking. She avoids book stores altogether so she doesn't have to see Exiled in the windows on display.

Eleanor finally comes clean at Thanksgiving that she has cancer. Blair doesn't turn to Chuck or Serena, instead she folds in upon herself. The next few weeks she feels heavier, like a storm is brewing and she can't do anything about it. .

Serena and Dan's sex tape is released and the floodgates open. Blair is so angry and hurt, she wants to scream until her lungs give out. And at the same time she is so tired she can't move. She feels seventeen again. She's so unhappy she doesn't know what to do, she hates this part of herself that she so effortlessly becomes when she's around Chuck and Serena.

So before history repeats itself and Serena shows up begging for forgiveness, Blair changes the ending. She won't lash out and declare war on her best friend, she won't even get mad.

It's the first snow fall of the year, the first of December, and Blair knew she would find Serena here, it's Serena's version of the duck pond. She's dressed warm, knees tucked underneath her, snuggled into the bench, protected from the blowing drifts of wet snow. Blair has a moment of deja vu, it's pouring rain, and they're in high school, crying as Blair bears her sole and they share the most honest moment of their friendship.

Blair showing up here is symbolic, and so beautifully poetic, except she's coming to remove the one thing she put in place five years before.

Serena freezes upon Blair's approach. Blair watches Serena have the same trip down memory lane before hesitantly smiling. Serena makes a move to get up.

"I can't be around you anymore, Serena." Blair says it so expressively without malice, that Serena's jaw drops and she falls back against the bench.

"What do you mean Blair? We're family remember? I love you, I will always love you." Serena replies quietly, looking down at her hands, probably thinking about the consequences of Blair's confession.

Blair sits down next to her, "And maybe that's the problem. We hold on to each other so tightly that it's stopping us from growing up and being the people we are meant to be."

"Blair I'm so sorry for what I did, I've just been so lost this last year, and I acted without thinking. I just need your help, the nonjudgmental breakfast club remember? We forgive each other for everything." Serena's plead is half hearted, because this has been a long time coming. Serena's never been as strong as Blair, and now that Blair had initiated it, Serena was grasping to hold on knowing she would fail.

Blair is still so composed, her entire life had become trite and the energy to keep it maintained was waning. She looks at Serena before continuing, "I've always been jealous of you and I when I tell you that you don't earn the things you get, it's only because I know how much you hate it."

"And I hate that you might be right, and I take what's yours, because I can." Serena says looking defeated.

"We've been too afraid to admit that our friendship hasn't been real in quite some time. It's what we've always known. I care about you, but… I like it when you're struggling. I feel insecure when you're successful and that's not right. It's not healthy. "

"So what now? We go on and forget about each other? I love you B, I always will." Serena gives Blair's hand a squeeze before letting go just as quickly.

"I love you too S. Maybe one day we can reconnect, make sure our children don't make the same mistakes we do." Blair is already getting up, turning to leave.

Before she can though, Serena calls back to her. "B, since we're being honest, I did it because I saw how happy you were with Dan."

Blair turns back, "Excuse me?"

"I know I accused you of not getting over Chuck, but the truth is Blair, you were getting over him. You and Dan were moving on, finding yourselves, without the rest of us, and I was angry and jealous. I manipulated him, so I could ruin your happiness." Serena looks exhausted, they both do. And this final declaration of truth is what finally ends their bond.

Blair smiles meekly waving her hand as if it doesn't matter, her eyes deceiving her that maybe this is what she had been afraid to hear the whole time. "I had already chosen Chuck, it doesn't matter now."

"But I put it in motion, and I just want you to know that you were happier than I'd ever seen you."

Blair looks down before meeting her eyes again. "Thank you, and S, I hope you can finally accept how bright your light is, don't let anyone stop you, including yourself from getting everything you want in life."

"I won't."

Blair walks away, the snow clinging to every inch of her the moment she walked out into the park, the invisible white flag tucked into her pocket.

She won't leave Chuck until he's on the right path, and so for two months she walks around on eggshells pretending everything is fine. Inside she wants to feel that motivation from the summer, she wants to be free.

"This isn't working Chuck."

"I knew it. I knew you would find some reason to turn your back on me again!"

"Can you honestly say you're happy with this relationship? We keep having the same arguments over and over, nothing gets resolved."

"Fine, leave. Just know, when you decide I'm worth being with again, I won't be here."

"I hope so. You deserve to be happy."

"Yeah, you too."

Before she leaves she thinks she hears him on the phone, "so much time wasted that could have been spent on the Empire."

If she had stayed a little longer she would have heard him say , "Thank you father, if I knew saying goodbye to Blair would have gotten me back in your graces, I would have done it a long time ago."

She spends the next couple weeks crying herself to sleep. And she's not sure if it's because she's finally let go of Chuck, or she's said goodbye to Serena. She starts to think it's beyond that, she cries for her baby, her mother's illness, and for Dan. She cries because for the first time in her life she has no one, fake or other. She can't hide behind her mask, or seek out counsel in Brooklyn, she has to face this on her own.

She hates Dan, for the ugly truths about his book that she wished weren't true. She misses him for being the only one to show her the light when he wasn't even there any more. She loves him even though it's too late.

She goes on though. She still has school and she focuses her energy into helping her mother, and learning everything she can, spending all of her vacations in Paris with her family. She seeks help from a therapist, and she's on her own for the first time in her life.

* * *

Blair was right on time as usual, never early and never late. It was February in New York, she was into her second month at her new job as editor in chief of W magazine, an accomplished task at the age of 40. She had been working non stop for nineteen years, or her entire life really. She managed to leave at a decent hour for being a Monday and was glad she was able to make it to drinks with a friend she hadn't seen in six months.

Her friend was already there of course, sitting in a secluded booth, drinks on the table. She was wearing Louboutin pumps and a Dolce and Gabbana couture that Blair almost considered calling a photographer so they could add her to this month's issue.

"Thank god you're here, I've had the longest day, I didn't expect it to be this hard to hire competent fashionable people," Blair spoke before gracefully sliding into the booth across from her friend.

"You just started, as soon as you mold them to your liking, no one will be able to stop talking about your strategic and powerful regime." Her friend lifted her dirty martini in salute, clinking it to Blair's own raised glass, and they both smirked before taking a sip.

"I'm glad you could meet me before you left, when's your flight?" Blair asked.

Checking her watch, her friend replied, "I need to leave for JFK in an hour."

"Sooo… how did the meeting go?" Blair looked at her impatiently as if she had expected the answer as soon as she sat down.

"They picked up my pilot, you're looking at the new show runner and director of Manhattan Elite."

"Congratulations! That's fabulous…" Blair was genuinely happy, it meant she would see more of her friend now that she would be in New York permanently. But the way she had replied made her think her friend wasn't as enthusiastic as her. "Wait, why don't you look excited, I thought you wanted to move to New York, get away from all those boho vegan Californians?"

"I would love to settle in here, be closer to the family, have the kids go to school in the city … it's Dan." Her friend replied, her gaze lingering into space.

"Cassandra, just because he avoids New York like the plague-"

Cassandra interrupted her before she could finish, "No, that's just it. He's corresponded with the editor at The New Yorker for years and apparently he's retiring and he's asked Dan to come interview for it. Dan wants to come home. And he told me he's still in love with me and wants to try again."

"Finally." Blair wasn't surprised. After becoming closer with Cassandra after her split with Dan three years prior, she had been waiting for the day Cassandra told her they were getting back together.

Cassandra looked at her questioningly.

Blair went on, "Come on, you tell me he hasn't dated anyone seriously in the three years you've been divorced. Anyways, how did you respond? I thought things with Bobby were getting more serious?"

Cassandra had begun dating her former childhood sweetheart, a man who brought a whole lot of baggage. Someone, she imagined, Dan Humphrey hated for a whole lot of reasons including the fact that he was probably reminded of Chuck Bass.

Cassandra sighed, taking another sip of her drink, "I didn't say anything, I just left. And I hated myself as soon as I did it."

Blair winced thinking about his incredibly bad track record with women leaving him after he professes his love to them. "That man should just never say I love you first."

"Exactly, and we've managed to stay such good friends since splitting, and the last two years, it's like he's a different person. He's so solid and secure, why do men always wait until after you divorce them to become the man you always wanted them to be?" Cassandra replies frustrated, knocking back the rest of her martini.

"It takes losing someone to make you realize what you've always needed." Blair replies looking off into space before taking an extra long sip of her own martini.

"Apparently, but then there's Bobby. I spent fifteen years pretending like he didn't exist, and then he pops back in my life and he hasn't gone away since. He is Teddy's father, and I can't help but love him too."

Blair was thankful in that moment, for choosing Chuck all those years before, for knowing that she would never look back in her life and wonder what could have been with them. She doesn't know much about Bobby and their relationship, and she wonders if Bobby is Blair's Chuck or Blair's Dan, because if she knew then the answer was obvious.

Blair replied thoughtfully, "And you've been dating him for awhile now. From my experience, if you're having doubts, you need to address them, because there is a reason they are there. And for the record, the only thing lamer than marrying Dan Humphrey, is divorcing Dan Humphrey and walking away from a second chance." She shrugged and waved her hand nonchalantly as if her confession wasn't as meaningful as it sounded.

Cassandra smiled at her, they had an unspoken bond when it came to her ex husband. "I caught him watching Rosemary's Baby the other week, he was mouthing the words. For years he refused to watch it. He said he couldn't stand the movie but he would never tell me why he owned it. And he's closer with his family, Nate, Vanessa, even Serena, than he was the entire time we were married. It's almost like he's made peace with whatever inner turmoil he had."

"That's good." Blair said meekly, she tried not to get too much detail on the inner workings of his life.

Cassandra took notice and switched the subject. "Enough about me. Men suck, what's new with you? How is Holly?"

They lost track of time talking, laughing, gossiping, and feeling ten years younger. Cassandra was up on her feet when she realized she should have left twenty minutes ago for the airport.

"I'll be back in the city in May, shooting starts in July! I need you superior taste in real estate." Cassandra says as their walking out the front door into a rainy New York night.

"I leave for Paris April 15, but I'll be back the end of August. In the meantime, I'll e-mail you anything I find!" Blair gives her a quick hug before they both start walking briskly to their destinations.

"You're the best. See you on the Upper East Side." Cassandra nods before ducking her head into her town car.

Blair feels an urge to ask her one last thing, "Cassandra, what are you going to do?" Blair semi shouts turning back from the open door of her own car.

Instead of replying Cassandra just winks at her, and replies "Ciao," before blowing her a kiss and disappearing down the street.

Blair finds out about the accident the next morning.

* * *

**I hope this isn't confusing. Second part takes place just before Dan moves back to the city. Blair and Cassandra are friends? And how long have they known each other? And also, as much as I love Blairena, they haven't been true friends for so long, they need a long break from one another. Thanks for reading, drop a line!**


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